| RESEARCH |
Stable carbenes with N, P atoms All stable singlet carbenes reported thus far have featured either an amino or a phosphino substituent. The unusual stability of these species is due mainly to electron donation from the nitrogen or phosphorus lone pair into the formally empty pp orbital of the carbenic center. Now, chemistry professor Guy Bertrand of Paul Sabatier University in Toulouse, France, and the University of California, Riverside, and coworkers have prepared a family of stable hybrid molecules: (amino) (phosphino)carbenes [J. Am. Chem. Soc., 124, 6806 (2002)]. One member of the family (shown here) can be stored in solution at 0 °C for a few days. This carbene, though, can be used to make related carbenes that are stable at room temperature. For example, the carbene shown reacts with elemental sulfur (S8) to give the corresponding carbene having a P=S bond. This and other results "demonstrate that a carbene moiety has now to be considered as an ordinary functional group, readily tolerating chemical transformations at its periphery, without itself becoming involved," the researchers write |
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